Process of preparing anthraquinone compounds.



" in le epeelllee UNITED STATES ROLAND HEINRICH SCHOLL.'OF KARLiRUHE, AND MAX MANNIIEIM, GERMANY, ASSIGNORS 'lO BADISCHE ANIMN e. SODA FA- PATENT OFFICE.

ALBERT item, or

ERIK, OF 'LUDWIOSHAFEN-ON-THE-RHINE, GERMAN Y, A CORPORATION.

P806!!! OF PHIPAHINQ ANTHIAQUINONI OOMPOUNOI- lpaetloattea ollnttarehtent lnlleetlea nu l'eiraeryldfll. larlel Ia mm.

' rum-c Ieb. so, 1001.

heim in the Grand Duchy of Baden, German d to Empire, have invented new and uee lul imrovementa in lroceaaes for Preparing Anihraqulnone con poundn ct which the hollow- "ll. n the epechication of the a7pplleetion ice :5 Lettere Patent Serial .\'o. 299, 76, tiled February 0, 1900, ie deacribed a newcleee of compoundenamely, than in which two anthrauinone reaiduea are combined together.

compounds are there called "dtanthreee uinon l" .compounda, end thcv are preaand y heating a halogen anthraquinone with e metal-euch, for instance, as copperhae the power of withdrawing the a; i e have now discovered a new process whereby theae eame dienthraquinonvl coma can be obtained I In carrying out our invention we treat a dieae anthraqumone compound with a metal, an that the dinzo o mm are eplit oil and the reeidnee comtogether. For inetance, in order to obmhe 2.2-dlntcthyl-l.l'-diautl uinonyl le claimed apeeilically in the a womenapoeiiication, we convert l-amido-lg5 moth thraquinene into ite dine aullate and t treat this with copper in the reeqiee of acetic anhydrid whereupon the iaao group ia aplit oil and the named dianthra quinon lcompound ielorm ee The ollowmg exanlplca will nerve to lurther llluetrate the nature of our invention ,ad the method of earryi it into practical theae l nvention not confined to examp we. The parta are by weight.

.5 E.-: .unplc l: Diesolve twenty parte of lminded-motttyl-unthraquinone in two huh-- tired and fifty (250) parts of aull'urie acid (containing ahoot ninety-cove (97) per cent. of ll, SO.) and add gradually-,while stire ring, at ordin'a temperature eight (8) perta a sodium nitrite. Ae econ ac a teet portion ahowe that no unconverted amide compon prcaeut pour the dieeo aolution onto five hundred (600) arts of ice, allow it toutand for three (3) ioura, lilter oil the dieao eullate with the aid of the pum and weeh with a little cold water, elcoho and ether, and allow to dry in the air. Then stir in ten (10) of 2-methyl-l-diaao-anthraquinone 9 ate with sixty (60) parte of acetic anhydrid and add two (2) perteof coppcrpower, whereupon cvolutionof nit 'cn takea place and a violeteolution ia obtained from which alter a few houre e yellowish-white precipitate aeperatee. Warm for a abort 7 time on the water-bath, illtcr with the aid 0! the pump, and euepend the precipitate in hot water In order to dcatrov any acetic enhvdrid which nzey hopreeent. Then trcatwithdilutc nitric acid in order to dieeolvc any copper powder, and tilter oh the 2.2-dimethyl-l.l'- dianthraquinonyl which is thus obtained in a pure form. e

Example 2: Dleeolre twenty-live parte of l-emido-authrequinone m two himdred and lift "(260)parta of ninety-nix (06) per cent. and rie acid and wltile at ordinary temperature add a solution 'of aeven and eevem-tenthe (7.?) parte ol eodiurn nitrite in one hundred (I00) parta of ninety-eix (06) Mar cent. eull'u ric aeid. .Pour the diaao eoltion ao obtained onto five hundred (500) parte of ice. allow it to atand for from three (3) to tour (4) home, filter and waeh with eleven (ll) percent. aullurie acid and then with acetone. Introduce the preae-calro, which ia atill damp with acetone, gradually, while atirring, into a mixture of one hundeed (100) arta of acetic anhfdrid and live (5) parte 0 copper powder. I the reaction doea not act in epontanemialy, warm the mixture ali htly; but to avoid a too violent reaction t to temperature ahould not riee above fort (40) d pree e-celte ie centi rade. After the two (2) to three (3 home, tilter oil and waeh with-aceticv l Introduce the product into water at a temperature of lift degrees centigre le, decent from un I added an the evolution of nitrogen ceeeee continue atirrmg for from red copper, filter, and waah with hot water. 7

it The'hl fillllllll-I'MltllllOltYl ao obtained can recryetallized from nitrobenaene and lorma a greeniah-yellow t ine powder which vea concentrated oethreel 3; Ii: (90) prr cent. enll'uric emd lull a I use Example 3: Dileelve one hmdretl (100) rte of z-roetkg-l-emido-enthrq ulnone it oh: hunrlml oi ninety-ll: (00) cent. eullu pan: odd of ort 40 e o In m in our 5 hunllred ports of ninety-nix (96) per cent. eulhirie eeld. end then pour the dune eohttion lo omnineti onto twelve hundred (1200 of ice. Allow to stood for houre. hlter oi! the dim eullete with e little oold water. eleohol,

ether end then allow it to driin the eir. the 2-methri-i mmhrequ one dieeo with eeetone and then introduce it, flit-ring, into 0 mixture pf four hun- (400) port: of poetic enhydrid end fif- (ll ports of zinc-hm. 'lhe'mixture It ea .wa think hruwn Kate, which alter e elmrl time lhliul he will tlv wormed no for ebout two (2) hours. Flirt-roll eml'then treet th warm water no order to remove a. lit lmllytlfill, Ill!" Mhlonc neul in order to removethe Sample 4; Direolve fifty (50) perte of 2 methyl- 1 -emi|loenthreqoinone eioehlo from 2-methyl-l-emldo4nthrehe by trretmrnt with eullur oxychloin live humlroal (500) pert: of ninetydienotine menu of e solution of fifteen (15) parts end iii

eotlium nitrito in two humlml (200) perte mutin -drown; por rout. mliuric mid.

Pom tlxe olem mlullon onto nine huru'nd (Ilium-tn o! ice nmi work up an ilrerribed t foregoing Example 1. Then slowly introduee the 'i-ehlor-2-met hyl 't-enthrequinone dieeo eulhte, while stirring, into .e

eeetic 'nnhytlrid. Evolution of nitrogen eoon takes place eml the mixture hecomel ,wnrrn. (ool externelly It) on to. keep the tem rat-ire helow thirty-five (35) tle cent e. Stir for 1 low houn at onion?- .n temperature lilter oll nml treat the m uct obteinetl en described in Exempe 2. The 4.4M!ichlor-2.2'-tlimethyl-I l '-1liunthruquinonyl e0 oh'teinetl commute of n yt'llmt powderwlueh dieeolvee in xylene, yi'elling o I yelldwIh-brown solution.

Now whet we 'cleim iel l. The prooeee for the production of on threq'uinone compound: by treating; dim. enthrequinono oompimnrl with e motel. 6K

2. The for tho production of no threquinone compmtmll by treating t diam. euthrequimme compound with coppnqmw 3. Die phrase for the prmluction of 2.2'- 0-. dimethyl-l.l'-clinnthrequmonyl by tn-etin' 2-methyl-enthrequinonr-l dim-sulfate with copper powder.

ln tretlmooy whereof we have llt'l'tlllllu Witnem:

J. Am. Loom, Joe. H. Lauri.

'euepenlirmoiten (l0 perteoleo der in one hundred elm lilty uw lm o set our head. in the presence of two mbacriho 5 

